Potassium Carbonate → Ethyl 4-({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)butanoate

Participants

Reaction Steps

The o-alkylation procedure described for 10 (example 5, step 2) was used. To a stirred suspension of 4-[(4-fluorophenyl)(3,3,5,5 tetramethylcyclohexylidene) methyl]phenol 9 (0.590 g, 1.74 mmol), K2CO3 (0.482 g, 3.5 mmol), and acetone (50 mL) was added ethyl 4-bromobutyrate (0.62 mL, 4.4 mmol) under a nitrogen atmosphere at RT. The reaction mixture was refluxed for 6 h, cooled to RT and filtered. Standard work-up followed by purification afforded 0.712 g (90%) of compound 12 as a white foam. 1H NMR (300 MHz, CDCl3): δ 7.14 (d, J=5.7 Hz, 1H), 7.11 (d, J=5.7 Hz, 1H), 7.07 (d, J=8.7 Hz, 2H), 6.98 and 6.95 (dd, J=8.7 Hz, J2=8.7 Hz, 2H), 6.81 (d, J=8.4 Hz, 2H), 4.16 (q, J=7.2 Hz, 2H), 3.99 (t, J=6.00 Hz, 2H), 3.49 (t, J=6.3 Hz, 2H), m, 2H), 2.11 (quint., J=6.30 Hz, 2H), 2.00 (s, 2H), 1.96 (s, 2H), 1.31 (br s, 2H), 1.27 (t, J=7.2 Hz, 3H), 0.95 (s, 6H), 0.94 (s, 6H). LCMS (ESI): m/z 475 (M+Na)+.

Provenance & Evidence